Story First, Logo Later: Building a Brand That Feels Human
When I sat down with Jason Ing, CMO of Gusto, I expected insights into brand and marketing strategy—and we got plenty of that. But what really stuck with me was something far more personal, and honestly, more powerful:
“Every business has a story. That’s what makes it compelling. Your origin story is your brand.”
That hit hard.
As a founder myself, I know how easy it is to get caught up in the product, the growth, the next problem to solve. But Jason’s point was simple and sharp: your story—the real one, the messy one, the reason-you-started-it-all one—isn’t a footnote. It’s your edge.
This episode was packed with insights like that. But before we dive in, a quick note on language:
When we say SMB, we’re talking about Small and Medium-sized Businesses—the cafés, restaurants, construction crews, manufacturers, retail stores, and service operators that make up the backbone of the real-world economy. These aren’t faceless corporations. They’re often family-run. They’re personal. And they’re powered by people showing up every day to serve their communities.
I believe SMBs don’t just belong in the brand conversation—they can actually lead it.
Here’s what I learned from Jason about how.
Why Brands Win (And Why SMBs Have the Advantage)
Jason’s career spans P&G, Microsoft, Xbox, Amazon, AWS, and now Gusto. So when he talks about what makes a brand work, I listen. One of the biggest takeaways? The best brands feel human.
At Gusto, they’ve built a product that helps small businesses run payroll, handle benefits, and manage their teams. But the magic isn’t just in the software—it’s in the way they do it. They name their characters. They create delight. They show up like a partner, not a utility.
“Small business owners are human. They’re taking risks for reasons bigger than money. And they deserve software that feels like it gets them.”
That mindset—serving customers with empathy and joy—is what separates great brands from the forgettable ones. And here’s the kicker: you don’t need a massive budget to do this. SMBs are actually better positioned to create these emotional connections.
Founders: Your Story Is the Brand
One of my favorite parts of our conversation was when Jason talked about how storytelling unlocks brand loyalty. He pointed to the Old Spaghetti Factory, where they literally print their founder story on the placemats. That detail stuck with both of us.
“You want to build trust? Tell people why you started.”
It sounds so obvious, but how many businesses actually do this? We hide behind taglines and logos, when the real differentiator is sitting right there in our founding story.
Think about your favorite local café, barbershop, bakery—what makes them special? It’s not just the coffee or the haircut. It’s the feeling. The personal touch. The “this is why we do it” vibe. And as Jason pointed out, human beings are drawn to stories.
So if you’re an SMB owner, here’s my challenge to you (and to myself): stop burying your story. Put it on the wall. Share it with your team. Put it in your product. Make it impossible to forget why you exist—and invite people to root for you.
What to Do When Things Go Wrong
Of course, building a strong brand isn’t just about the highs. We talked about the hard stuff too—like what to do when a customer leaves a bad review or something breaks down in your service.
Jason’s advice? Don’t ignore it. Don’t get defensive. Fix it fast, and use it as a signal.
“Acknowledge the issue. Show you care. And turn that moment into trust.”
One thing I loved about his perspective was how much he referenced systems—drawing from Amazon’s operational rigor and the idea of treating negative feedback like a defect. Diagnose it. Solve the root cause. And when possible, turn your happiest customers into your loudest advocates.
Leadership Is What You Do, Not Just What You Say
We also dug into leadership. Jason’s view? It’s what you do, not just what you say.
It’s not about being the loudest voice or the person with all the answers. It’s about character. Judgment. How you show up when things get hard. And in the SMB world—where staffing issues, stress, and uncertainty are daily realities—that kind of leadership matters more than ever.
I asked him what advice he’d give to any operator running a small business, and he didn’t hesitate:
“Know your customer. Know them so well that they feel like fans, not just customers.”
That right there? That’s the unlock. Whether you’re serving coffee, cutting hair, or building software, people are your power. And the best brands and leaders never forget that.
On AI, Speed, and the Future of Marketing
Jason sees AI as a lever, not a threat. For marketers, founders, and operators alike, tools like generative AI can take a lot of the friction out of building and iterating—and they level the playing field.
“AI won’t kill marketing. But it will kill bad marketing.”
He sees it as a way to make everyone better—faster. The brands with something real to say will rise above the noise, and the ones just going through the motions? They'll get left behind.
My Favorite Moment: Jason on Career Planning
I asked Jason what question he wishes people asked him more. His answer was gold:
“People ask me all the time, ‘How do I become a CMO?’ or ‘What’s your five-year plan?’ I don’t have one. The truth is, life punches you in the face. You need a North Star, but you can’t prescribe every step.”
That stuck with me. Whether you’re managing a team, building a brand, or just trying to grow your business—it’s not about having the perfect path. It’s about showing up. Giving yourself enough at-bats. Staying flexible.
Final Thoughts: If You’re Building Something, Tell Us Why
There’s a lot I’ll take from this conversation. But the core lesson is this:
The best brands—and the best leaders—are the ones that feel real.
If you’re building something, running something, or leading a team, lean into your story. Share it. Show up with consistency, humility, and care. That’s how you build trust. That’s how you create something worth remembering.
Thanks again to Jason for being such a generous and insightful guest. This one will stick with me for a long time.
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